Diisopropylethylamine → HCID 86650468, compound

HRID 240196Notes

Reaction equation

HRID 240196 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[O:19][C:18](=[O:21])[C:17]([C:22]([OH:24])=O)=[CH:16]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:49]([O:53][C:54]([N:56]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH:58]=[C:57]1[C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([NH2:71])[CH:66]=1)=[O:55])([CH3:52])([CH3:51])[CH3:50]>CN(C=O)C>[C:49]([O:53][C:54]([N:56]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH:58]=[C:57]1[C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([NH:71][C:22]([C:17]2[C:18](=[O:21])[O:19][C:20]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[OH:10])=[O:24])[CH:66]=1)=[O:55])([CH3:52])([CH3:50])[CH3:51]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 72457168-Hydroxy-3-carboxy-coumarinHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66865725HCID 66865725, compound

Product 1

HCID 86650468HCID 86650468, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.012 mL, 0.071 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.013 g, 0.065 mmol) and HATU (0.027 g, 0.071 mmol) in 0.5 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 2-(3-Amino-phenyl)-indole-1-carboxylic acid tert-butyl ester (0.02 g, 0.065 mmol) was added and allowed to react overnight. DMF was removed under vacuum and the reaction was resuspended in DMSO. The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage) using a solvent gradient of 10-95% ACN/H2O with 0.05% TFA at a flow rate of 20 mL/min. UV absorbance was monitored at 254 nm and the fractions corresponding to the product peak were collected and the solvent removed under vacuum to give 0.02 g of product in 64% yield: LCMS (ESI) m/z 497 (MH+).

Workup

  1. customresulted
  2. customto react overnight
  3. customDMF was removed under vacuum
  4. customThe crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage)
  5. customthe fractions corresponding to the product peak were collected
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-2c065d67c8984631adfc26f73fc1af0c
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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